Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility

Viktor Barát; Maja Budanovic; Si Man Tam; June Huh; Richard D. Webster; Mihaiela C. Stuparu

doi:10.1002/chem.201905521

Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility

Viktor Barát, Maja Budanovic, Si Man Tam, June Huh, Richard D. Webster^*, Mihaiela C. Stuparu

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C₁₈H₃₇) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.

Original language	English
Pages (from-to)	3231-3235
Number of pages	5
Journal	Chemistry - A European Journal
Volume	26
Issue number	15
DOIs	https://doi.org/10.1002/chem.201905521
Publication status	Published - Mar 12 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Organic Chemistry

Keywords

corannulene
electron-deficient compounds
fused-ring systems
polycyclic aromatic hydrocarbons
sulfones

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10.1002/chem.201905521

Cite this

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title = "Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility",

abstract = "It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C18H37) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.",

keywords = "corannulene, electron-deficient compounds, fused-ring systems, polycyclic aromatic hydrocarbons, sulfones",

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doi = "10.1002/chem.201905521",

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T2 - Combining Modular and Practical Synthesis with Electron Affinity and Solubility

AU - Barát, Viktor

AU - Budanovic, Maja

AU - Tam, Si Man

AU - Huh, June

AU - Webster, Richard D.

AU - Stuparu, Mihaiela C.

PY - 2020/3/12

Y1 - 2020/3/12

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AB - It is shown in this work that high electron affinity can be combined with high solubility and practical accessibility in corannulene-based electron acceptors. The electron affinity originates from the presence of three different types of electron-withdrawing groups (imide, sulfone, and trifluoromethyl) on the aromatic scaffold. The imide substituent further hosts a long alkyl chain (C18H37) to boast solubility in a wide range of organic solvents. The synthesis is modular and consists of three simple steps from a commonly available corannulene derivative with an overall isolated yield of 22–27 %.

KW - corannulene

KW - electron-deficient compounds

KW - fused-ring systems

KW - polycyclic aromatic hydrocarbons

KW - sulfones

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Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and Solubility

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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